Isophthalaldehyde

Isophthalaldehyde
Names
	Other names 1,3-Benzenedialdehyde, 1,3-Diformylbenzene
Identifiers
CAS Number	626-19-7 ;
3D model (JSmol)	Interactive image;
ChEMBL	ChEMBL2289228;
ChemSpider	32002;
ECHA InfoCard	100.009.942
EC Number	210-935-8;
PubChem CID	34777;
UNII	LU162B2N9X;
CompTox Dashboard (EPA)	DTXSID30870718 ;
	InChI InChI=1S/C8H6O2/c9-5-7-2-1-3-8(4-7)6-10/h1-6H Key: IZALUMVGBVKPJD-UHFFFAOYSA-N;
	SMILES C1=CC(=CC(=C1)C=O)C=O;
Properties
Chemical formula	C8H6O2
Molar mass	134.134 g·mol−1
Appearance	white
Density	1.395 g/cm3
Melting point	89.5 °C (193.1 °F; 362.6 K)
Hazards
	GHS labelling:
Pictograms
Signal word	Warning
Hazard statements	H315, H319, H335
Precautionary statements	P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, P501
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Isophthalaldehyde is an organic compound with the formula C₆H₄(CHO)₂. It is one of three isomers of benzene dicarbaldehyde, a reduced analog of phthalic acid. It is a colorless solid, although commercial samples often appear yellowish. One preparation entails the Sommelet reaction of α,α'-diamino-ortho-xylene.^[3]

Reactions and use

Like many benzaldehydes, isophthalaldehyde forms a variety of Schiff base derivatives. Being bifunctional (having two formyl groups), isophthalaldehyde allows the formation of polymers or covalent organic frameworks upon reaction with di- or triamines.^[4] ^[5] They also find use in metal coordination complexes.^[6]

Related compounds

References

^ Britton, Doyle (2002). "O- andm-Benzenedicarbaldehyde". Acta Crystallographica Section C Crystal Structure Communications. 58 (11): o637–o639. doi:10.1107/S0108270102015597. PMID 12415166. S2CID 7685455.
^ "Isophthalaldehyde". pubchem.ncbi.nlm.nih.gov. Retrieved 3 February 2022.
^ Ackerman, J. H.; Surrey, A. R. (1967). "Isophthalaldehyde". Organic Syntheses. 47: 76. doi:10.15227/orgsyn.047.0076.
^ Schwab, Matthias Georg; Fassbender, Birgit; Spiess, Hans Wolfgang; Thomas, Arne; Feng, Xinliang; Müllen, Klaus (2009). "Catalyst-free Preparation of Melamine-Based Microporous Polymer Networks through Schiff Base Chemistry". J. Am. Chem. Soc. 131 (21): 7216–7217. doi:10.1021/ja902116f. PMID 19469570.
^ Schoustra, Sybren K.; Smulders, Maarten M. J. (2023). "Metal Coordination in Polyimine Covalent Adaptable Networks for Tunable Material Properties and Enhanced Creep Resistance". Macromolecular Rapid Communications. 44 (5): 2200790. doi:10.1002/marc.202200790. PMID 36629864. S2CID 255593988.
^ Nasr, G.; Macron, T.; Gilles, A.; Mouline, Z.; Barboiu, M. (2012). "Metallodynameric membranes – toward the constitutional transport of gases". Chemical Communications. 48 (54): 6827–6829. doi:10.1039/C2CC32656F.

[1] Britton, Doyle (2002). "O- andm-Benzenedicarbaldehyde". Acta Crystallographica Section C Crystal Structure Communications. 58 (11): o637–o639. doi:10.1107/S0108270102015597. PMID 12415166. S2CID 7685455.

[2] "Isophthalaldehyde". pubchem.ncbi.nlm.nih.gov. Retrieved 3 February 2022.

[3] Ackerman, J. H.; Surrey, A. R. (1967). "Isophthalaldehyde". Organic Syntheses. 47: 76. doi:10.15227/orgsyn.047.0076.

[4] Schwab, Matthias Georg; Fassbender, Birgit; Spiess, Hans Wolfgang; Thomas, Arne; Feng, Xinliang; Müllen, Klaus (2009). "Catalyst-free Preparation of Melamine-Based Microporous Polymer Networks through Schiff Base Chemistry". J. Am. Chem. Soc. 131 (21): 7216–7217. doi:10.1021/ja902116f. PMID 19469570.

[5] Schoustra, Sybren K.; Smulders, Maarten M. J. (2023). "Metal Coordination in Polyimine Covalent Adaptable Networks for Tunable Material Properties and Enhanced Creep Resistance". Macromolecular Rapid Communications. 44 (5): 2200790. doi:10.1002/marc.202200790. PMID 36629864. S2CID 255593988.

[6] Nasr, G.; Macron, T.; Gilles, A.; Mouline, Z.; Barboiu, M. (2012). "Metallodynameric membranes – toward the constitutional transport of gases". Chemical Communications. 48 (54): 6827–6829. doi:10.1039/C2CC32656F.

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